Wash Sale

[BryanMD]

I've fired my financial advisor and have taken over my own financial life in the last month. I had a lot of money sitting in cash that I started to get working in the Vanguard total market index ETF(VTI). This is giving me some great practice at tax loss harvesting in the last couple of weeks unfortunately.

My question is about tax loss harvesting when you've bought the same index fund in two different accounts. I bought VTI in a taxable account as well as some in my Roth IRA. I bought both batches around the same day. Do I need to sell all of the VTI to be able to tax loss harvest? Do the shares in the Roth IRA count as a wash sale since I bought them within 30 days of the shares in the taxable account. In the taxable account I sold all of the VTI and bought iShares Total Market ETF (ITOT) and booked about $9k in losses, but I didn't sell the much smaller amount of VTI in my Roth account. I'm thinking of now selling all of that ITOT and booking another $6k in losses as I exchange it for the Fidelity Total Market Fund (FZROX). Should I sell the Roth VTI shares for the FZROX shares at the same time just to make sure it doesn't set off a wash sale with that first tax loss harvest?

[BryanMD]

With some deeper searching I think I may have found my answer that yes, I do need to sell the VTI shares in my Roth IRA. My new question is does this have to be done at the same time as the original TLH with the VTI sell in my taxable account? Can I go in and sell those Roth VTI shares now a week later and avoid that wash sale? What is the time limit to sell all the VTI shares?

[childay]

You are correct on my brief take. Sell the Roths also and you're good. It's 30 days before and after the sale for loss. So as long as you sell all lots in that time frame you're good
I'm in similar boat with the recent backdoor Roth contributions, annoyingly

[BryanMD]

I, of course, would have preferred to watch my investments go up after ditching my financial advisor. But it is a little satisfying to book some losses to carry forward over the next few years. My advisor didn’t really do much TLH for me in March 2020.

[childay]

I, of course, would have preferred to watch my investments go up after ditching my financial advisor. But it is a little satisfying to book some losses to carry forward over the next few years. My advisor didn’t really do much TLH for me in March 2020.

Absolutely $15K in losses sounds worth doing I didn't have that much loss today and then realized the Roths would be a wash so I'll procrastinate some more

Also will look into the zero fund with unique index didn't really think about it for tlh in past